Iodine → HCID 87213766, compound

HRID 2249381Notes

Reaction equation

HRID 2249381 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[O:10][CH3:11].C([Li])CCC.[I:17]I>C1COCC1.C(OCC)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([I:17])=[C:4]([F:9])[C:3]=1[O:10][CH3:11]

Participants

7

Reactant 3

HCID 807IodineHCID 66953855HCID 66953855, compoundHCID 178418339Butyllithium

Product 1

HCID 87213766HCID 87213766, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 24477Sodium ThiosulfateSolvent

Conditions

Temperature
-75 °C

Procedure

To a solution of 1-chloro-3,5-difluoro-2-methoxybenzene (2.0 g, 0.01 mol) in THF at −75° C. was added n-butyl lithium (2.5M in hexanes 6.7 mL) and the resulting solution was stirred at −75° C. for 1 hour. A solution of iodine (5.1 g, 0.02 mol) in THF (10 mL) was added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was diluted with ethyl ether (50 mL) and aqueous sodium thiosulfate (10%, 50 mL) was added and stirred for 1 hour. After separating the phases, the organic phase was dried (Na2SO4) and concentrated to give 1-chloro-3,5-difluoro-4-iodo-2-methoxybenzene as a white solid: mp 62-64° C.

Workup

  1. temperatureto warm to ambient temperature
  2. additionwas added
  3. stirringstirred for 1 hour
  4. customAfter separating the phases
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8fce46ec5e6147f3a7bba21479a5aa95
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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